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Preparation process of impurities contained in expectorant drug bromhexine hydrochloride

A technology of bromhexine hydrochloride and preparation process is applied in the preparation of organic compounds, the preparation of amino compounds, the preparation of amino-substituted functional groups, etc., and can solve problems such as low purity and high price

Inactive Publication Date: 2015-02-18
HEBEI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The impurity C, impurity D and impurity E sold in the market are all imported from abroad, and the purity is not high, the price is expensive, and there are no relevant literature reports on the synthesis methods of these impurities

Method used

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  • Preparation process of impurities contained in expectorant drug bromhexine hydrochloride
  • Preparation process of impurities contained in expectorant drug bromhexine hydrochloride
  • Preparation process of impurities contained in expectorant drug bromhexine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] The preparation process of the impurity contained in the expectorant medicine bromhexine hydrochloride of embodiment 1

[0077] (1) Preparation of impurity C

[0078]

[0079] ①The preparation of intermediate anthranilic acid chloride

[0080] Add 5mL of thionyl chloride into a 10mL reaction flask, cool down to 10-20°C, add 1g of anthranilyl alcohol, raise the temperature to 40°C and stir for 1 hour, TLC monitors that the reaction is complete, distill off the thionyl chloride, and the obtained solid is 35°C Vacuum drying for 2 hours gave the target anthranilic acid chloride as a yellow solid;

[0081] ② Impurity C, namely the preparation of N-methyl-N-cyclohexyl-2-aminobenzylamine

[0082] Add 1mL of ethyl acetate and 1.1g of N-methylcyclohexylamine into a 10mL reaction flask, add 0.75g of anthraniloyl chloride, stir and react at 35°C for 2h after the addition, add 2mL of absolute ethanol, heat up and reflux for 0.5h , filtered while hot, the filtrate was rotary e...

Embodiment 2

[0129] The preparation technology of the impurity contained in embodiment 2 expectorant medicine bromhexine hydrochloride

[0130] (1) Preparation of impurity C

[0131]

[0132] ①The preparation of intermediate anthranilic acid chloride

[0133]Add 5mL of phosphorus oxychloride into a 10mL reaction flask, cool down to 10-20°C, add 1g of anthranilobenzyl alcohol, raise the temperature to 40°C and stir for 1 hour, TLC monitors that the reaction is complete, evaporate the phosphorus oxychloride, and the obtained solid is 35°C Vacuum drying for 2 hours gave the target anthranilic acid chloride as a yellow solid;

[0134] ② Impurity C, namely the preparation of N-methyl-N-cyclohexyl-2-aminobenzylamine

[0135] Add 1mL of ethanol and 1.1g of N-methylcyclohexylamine into a 10mL reaction flask, add 1.5g of anthraniloyl chloride, stir and react at 30°C for 2h after the addition, add 2mL of absolute ethanol, heat up and reflux for 0.5h, and Filtrate hot, remove the solvent by rot...

Embodiment 3

[0165] The preparation process of the impurity contained in embodiment 3 expectorant medicine bromhexine hydrochloride

[0166] (1) Preparation of impurity C

[0167]

[0168] ①The preparation of intermediate anthranilic acid chloride

[0169] Add 5mL of phosphorus trichloride into a 10mL reaction flask, cool down to 10-20°C, add 1g of anthranilobenzyl alcohol, raise the temperature to 40°C and stir the reaction for 1h, TLC monitors that the reaction is complete, evaporate the phosphorus trichloride, and the obtained solid is 35°C Vacuum drying for 2 hours gave the target anthranilic acid chloride as a yellow solid;

[0170] ② Impurity C, namely the preparation of N-methyl-N-cyclohexyl-2-aminobenzylamine

[0171] Add 1mL of DMSO and 1.1g of N-methylcyclohexylamine into a 10mL reaction flask, add 0.37g of anthraniloyl chloride, stir and react at 35°C for 2h after the addition is complete, add 2mL of absolute ethanol, heat up and reflux for 0.5h, while hot Filtrate, remove...

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Abstract

The invention relates to a preparation process of impurities contained in an expectorant drug bromhexine hydrochloride and belongs to the field of pharmaceutical technology and medicinal chemistry. The preparation process comprises the steps of preparation of an impurity C, an impurity D, an impurity E, an impurity F, an impurity G and an impurity H and has the advantages that the purity of the impurities is high, the preparation method is simple, complex separation and purification methods are not needed and the gram-level sample can be prepared at one time, sufficient qualified references can be provided for the quality control of bromhexine hydrochloride, a guarantee is provided for improving the quality of the hydrochloride bromine drug and the primary problems that the references of impurities contained in bromhexine hydrochloride depend on import and the cost is very high are solved.

Description

technical field [0001] The invention relates to a preparation process of impurities contained in medicines, in particular to a preparation process of impurities contained in bromhexine hydrochloride, an expectorant drug, and belongs to the fields of medical technology and medicinal chemistry. Background technique [0002] Bromhexine hydrochloride is an expectorant drug, which can directly act on bronchial glands, promote the release of lysosomes in mucus-secreting cells, and make the sticky sugar fibers in sputum differentiate and crack; it can also inhibit the acidity in mucus glands and goblet cells. The synthesis of glycoproteins makes it secrete small molecule glycoproteins with low viscosity, so that the viscosity of sputum is reduced and it is easy to cough up. Clinically, bromhexine hydrochloride is used for acute and chronic bronchitis, asthma, bronchiectasis, and emphysema, especially for those who have difficulty coughing up white sticky sputum and critical emergen...

Claims

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Application Information

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IPC IPC(8): C07C211/49C07C209/68C07C211/52C07C209/00C07C209/08C07D239/74
Inventor 张恺石晓伟薛娜杜玉民王磊
Owner HEBEI MEDICAL UNIVERSITY
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